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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (3) Show 3 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:52:00 UTC

HMDB ID

HMDB0015500

Secondary Accession Numbers

HMDB15500

Metabolite Identification

Common Name

Allylestrenol

Description

Allylestrenol is only found in individuals that have used or taken this drug. It is a synthetic steroid with progestational activity. [PubChem]Allylestrenol is similar in structure and function to progesterone. Progesterone shares the pharmacological actions of the progestins. Progesterone binds to the progesterone and estrogen receptors. Target cells include the female reproductive tract, the mammary gland, the hypothalamus, and the pituitary. Once bound to the receptor, progestins like Progesterone will slow the frequency of release of gonadotropin releasing hormone (GnRH) from the hypothalamus and blunt the pre-ovulatory LH (luteinizing hormone) surge. In women who have adequate endogenous estrogen, progesterone transforms a proliferative endometrium into a secretory one. Progesterone is essential for the development of decidual tissue and is necessary to increase endometrial receptivity for implantation of an embryo. Once an embryo has been implanted, progesterone acts to maintain the pregnancy. Progesterone also stimulates the growth of mammary alveolar tissue and relaxes uterine smooth muscle. It has little estrogenic and androgenic activity.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

1431
  Mrv0541 02231215292D          

 26 29  0  0  1  0            999 V2000
    5.9104    1.6065    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3833    0.5700    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3833   -0.2550    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6689   -0.6675    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9544   -0.2550    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1640    0.8214    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6689    0.9825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1640   -0.5064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9544    0.5700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6455    0.1575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2036   -0.6731    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6821   -1.5268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3833    1.3950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9412   -1.9622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1970   -1.5325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8323    1.3052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4389   -0.2078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6570   -0.6433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4252   -1.9861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.5385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5854    0.9683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2537    1.4521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4532   -0.9113    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2430   -0.9931    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5260    0.0750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2163   -0.0133    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  1  0  0  0
  2  3  1  0  0  0  0
  2  6  1  0  0  0  0
  2  7  1  0  0  0  0
  2 13  1  1  0  0  0
  3  4  1  0  0  0  0
  3  8  1  0  0  0  0
  3 23  1  6  0  0  0
  4  5  1  0  0  0  0
  4 12  1  0  0  0  0
  4 24  1  1  0  0  0
  5  9  1  0  0  0  0
  5 11  1  0  0  0  0
  5 25  1  6  0  0  0
  6 10  1  0  0  0  0
  6 16  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
 11 15  1  0  0  0  0
 11 17  1  0  0  0  0
 11 26  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 19  2  0  0  0  0
 16 21  1  0  0  0  0
 17 18  1  0  0  0  0
 18 20  1  0  0  0  0
 19 20  1  0  0  0  0
 21 22  2  0  0  0  0
M  END

HMDB0015500
     RDKit          3D
Allylestrenol
 54 57  0  0  0  0  0  0  0  0999 V2000
    4.2127    2.2854    3.5034 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2191    1.9970    2.6549 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4543    1.3069    1.3782 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7586    0.0075    1.3076 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2328   -0.7586    2.4054 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3520   -0.8145    0.1083 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1537   -1.6322   -0.3078 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1229   -0.5836   -0.2296 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2944   -0.9918   -0.3768 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5472   -1.9731   -1.4834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0316   -2.2998   -1.4259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8150   -1.0429   -1.6096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8977   -1.0858   -2.3592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8005    0.0466   -2.6590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2592    1.3752   -2.2264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7661    1.3360   -1.9811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4291    0.2370   -0.9915 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0181    0.3271   -0.5389 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8548    1.1179    0.7194 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5022    1.1861    1.3089 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.0555    1.1862 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7780   -1.0631    2.2002 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2535    2.0132    3.2729 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9850    2.7896    4.4171 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2454    2.3147    2.9659 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5641    1.0840    1.3336 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2779    1.9652    0.4955 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2059   -0.5951    2.4372 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2304   -1.3723    0.3981 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5221   -0.0494   -0.6789 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2680   -1.9913   -1.3594 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0665   -2.4944    0.3485 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3659    0.2212   -0.9325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6702   -1.4382    0.5644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2082   -1.6503   -2.4695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0229   -2.9086   -1.1997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2199   -2.6358   -0.3759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3403   -3.1010   -2.0866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1786   -2.0460   -2.8188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8496   -0.1241   -2.2958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9030    0.0888   -3.7849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4752    2.2084   -2.9193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7833    1.6299   -1.2620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3152    1.0112   -2.9640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4023    2.3212   -1.6975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0705    0.4570   -0.0869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4550    0.8798   -1.3490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6473    0.8307    1.4535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1499    2.1796    0.4459 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0247    2.0799    0.9278 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3183    1.3253    2.4282 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4572   -1.0112    3.0745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2372   -0.8084    2.5641 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7719   -2.0955    1.8391 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  1
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  1
 21  4  1  0
 21  8  1  0
 18  9  1  0
 17 12  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  6
  9 34  1  1
 10 35  1  0
 10 36  1  0
 11 37  1  0
 11 38  1  0
 13 39  1  0
 14 40  1  0
 14 41  1  0
 15 42  1  0
 15 43  1  0
 16 44  1  0
 16 45  1  0
 17 46  1  1
 18 47  1  6
 19 48  1  0
 19 49  1  0
 20 50  1  0
 20 51  1  0
 22 52  1  0
 22 53  1  0
 22 54  1  0
M  END

1431
  Mrv0541 02231215292D          

 26 29  0  0  1  0            999 V2000
    5.9104    1.6065    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3833    0.5700    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3833   -0.2550    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6689   -0.6675    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9544   -0.2550    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1640    0.8214    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6689    0.9825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1640   -0.5064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9544    0.5700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6455    0.1575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2036   -0.6731    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6821   -1.5268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3833    1.3950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9412   -1.9622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1970   -1.5325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8323    1.3052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4389   -0.2078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6570   -0.6433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4252   -1.9861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.5385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5854    0.9683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2537    1.4521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4532   -0.9113    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2430   -0.9931    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5260    0.0750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2163   -0.0133    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  1  0  0  0
  2  3  1  0  0  0  0
  2  6  1  0  0  0  0
  2  7  1  0  0  0  0
  2 13  1  1  0  0  0
  3  4  1  0  0  0  0
  3  8  1  0  0  0  0
  3 23  1  6  0  0  0
  4  5  1  0  0  0  0
  4 12  1  0  0  0  0
  4 24  1  1  0  0  0
  5  9  1  0  0  0  0
  5 11  1  0  0  0  0
  5 25  1  6  0  0  0
  6 10  1  0  0  0  0
  6 16  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
 11 15  1  0  0  0  0
 11 17  1  0  0  0  0
 11 26  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 19  2  0  0  0  0
 16 21  1  0  0  0  0
 17 18  1  0  0  0  0
 18 20  1  0  0  0  0
 19 20  1  0  0  0  0
 21 22  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015500

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12CC[C@@](O)(CC=C)[C@@]1(C)CC[C@]1([H])[C@@]3([H])CCCC=C3CC[C@@]21[H]

> <INCHI_IDENTIFIER>
InChI=1S/C21H32O/c1-3-12-21(22)14-11-19-18-9-8-15-6-4-5-7-16(15)17(18)10-13-20(19,21)2/h3,6,16-19,22H,1,4-5,7-14H2,2H3/t16-,17+,18+,19-,20-,21-/m0/s1

> <INCHI_KEY>
ATXHVCQZZJYMCF-XUDSTZEESA-N

> <FORMULA>
C21H32O

> <MOLECULAR_WEIGHT>
300.4782

> <EXACT_MASS>
300.245315646

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
37.17381391662096

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,10R,11S,14R,15S)-15-methyl-14-(prop-2-en-1-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-ol

> <ALOGPS_LOGP>
5.14

> <JCHEM_LOGP>
4.828528498666667

> <ALOGPS_LOGS>
-5.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-0.17303499701586655

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
93.1439

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.58e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
gestanin

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0015500
     RDKit          3D
Allylestrenol
 54 57  0  0  0  0  0  0  0  0999 V2000
    4.2127    2.2854    3.5034 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2191    1.9970    2.6549 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4543    1.3069    1.3782 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7586    0.0075    1.3076 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2328   -0.7586    2.4054 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3520   -0.8145    0.1083 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1537   -1.6322   -0.3078 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1229   -0.5836   -0.2296 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2944   -0.9918   -0.3768 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5472   -1.9731   -1.4834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0316   -2.2998   -1.4259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8150   -1.0429   -1.6096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8977   -1.0858   -2.3592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8005    0.0466   -2.6590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2592    1.3752   -2.2264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7661    1.3360   -1.9811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4291    0.2370   -0.9915 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0181    0.3271   -0.5389 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8548    1.1179    0.7194 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5022    1.1861    1.3089 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.0555    1.1862 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7780   -1.0631    2.2002 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2535    2.0132    3.2729 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9850    2.7896    4.4171 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2454    2.3147    2.9659 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5641    1.0840    1.3336 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2779    1.9652    0.4955 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2059   -0.5951    2.4372 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2304   -1.3723    0.3981 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5221   -0.0494   -0.6789 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2680   -1.9913   -1.3594 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0665   -2.4944    0.3485 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3659    0.2212   -0.9325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6702   -1.4382    0.5644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2082   -1.6503   -2.4695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0229   -2.9086   -1.1997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2199   -2.6358   -0.3759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3403   -3.1010   -2.0866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1786   -2.0460   -2.8188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8496   -0.1241   -2.2958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9030    0.0888   -3.7849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4752    2.2084   -2.9193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7833    1.6299   -1.2620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3152    1.0112   -2.9640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4023    2.3212   -1.6975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0705    0.4570   -0.0869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4550    0.8798   -1.3490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6473    0.8307    1.4535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1499    2.1796    0.4459 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0247    2.0799    0.9278 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3183    1.3253    2.4282 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4572   -1.0112    3.0745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2372   -0.8084    2.5641 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7719   -2.0955    1.8391 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  1
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  1
 21  4  1  0
 21  8  1  0
 18  9  1  0
 17 12  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  6
  9 34  1  1
 10 35  1  0
 10 36  1  0
 11 37  1  0
 11 38  1  0
 13 39  1  0
 14 40  1  0
 14 41  1  0
 15 42  1  0
 15 43  1  0
 16 44  1  0
 16 45  1  0
 17 46  1  1
 18 47  1  6
 19 48  1  0
 19 49  1  0
 20 50  1  0
 20 51  1  0
 22 52  1  0
 22 53  1  0
 22 54  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1431                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      11.033   2.999   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      10.049   1.064   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.049  -0.476   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.715  -1.246   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.382  -0.476   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.506   1.533   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.715   1.834   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.506  -0.945   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.382   1.064   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.405   0.294   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.980  -1.256   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.740  -2.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.049   2.604   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.357  -3.663   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.968  -2.861   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.754   2.436   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.553  -0.388   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.093  -1.201   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.527  -3.707   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.080  -2.872   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      14.159   1.807   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      15.407   2.711   0.000  0.00  0.00           C+0
HETATM   23  H   UNK     0      10.179  -1.701   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0       9.787  -1.854   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0       8.449   0.140   0.000  0.00  0.00           H+0
HETATM   26  H   UNK     0       6.004  -0.025   0.000  0.00  0.00           H+0
CONECT    1    6                                                            
CONECT    2    3    6    7   13                                             
CONECT    3    2    4    8   23                                             
CONECT    4    3    5   12   24                                             
CONECT    5    4    9   11   25                                             
CONECT    6    1    2   10   16                                             
CONECT    7    2    9                                                       
CONECT    8    3   10                                                       
CONECT    9    5    7                                                       
CONECT   10    6    8                                                       
CONECT   11    5   15   17   26                                             
CONECT   12    4   14                                                       
CONECT   13    2                                                            
CONECT   14   12   15                                                       
CONECT   15   11   14   19                                                  
CONECT   16    6   21                                                       
CONECT   17   11   18                                                       
CONECT   18   17   20                                                       
CONECT   19   15   20                                                       
CONECT   20   18   19                                                       
CONECT   21   16   22                                                       
CONECT   22   21                                                            
CONECT   23    3                                                            
CONECT   24    4                                                            
CONECT   25    5                                                            
CONECT   26   11                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   58    0
END

COMPND    HMDB0015500
HETATM    1  C1  UNL     1       4.213   2.285   3.503  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.219   1.997   2.655  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.454   1.307   1.378  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.759   0.008   1.308  1.00  0.00           C  
HETATM    5  O1  UNL     1       3.233  -0.759   2.405  1.00  0.00           O  
HETATM    6  C5  UNL     1       3.352  -0.814   0.108  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.154  -1.632  -0.308  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.123  -0.584  -0.230  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.294  -0.992  -0.377  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.547  -1.973  -1.483  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.032  -2.300  -1.426  1.00  0.00           C  
HETATM   12  C11 UNL     1      -2.815  -1.043  -1.610  1.00  0.00           C  
HETATM   13  C12 UNL     1      -3.898  -1.086  -2.359  1.00  0.00           C  
HETATM   14  C13 UNL     1      -4.801   0.047  -2.659  1.00  0.00           C  
HETATM   15  C14 UNL     1      -4.259   1.375  -2.226  1.00  0.00           C  
HETATM   16  C15 UNL     1      -2.766   1.336  -1.981  1.00  0.00           C  
HETATM   17  C16 UNL     1      -2.429   0.237  -0.992  1.00  0.00           C  
HETATM   18  C17 UNL     1      -1.018   0.327  -0.539  1.00  0.00           C  
HETATM   19  C18 UNL     1      -0.855   1.118   0.719  1.00  0.00           C  
HETATM   20  C19 UNL     1       0.502   1.186   1.309  1.00  0.00           C  
HETATM   21  C20 UNL     1       1.299  -0.056   1.186  1.00  0.00           C  
HETATM   22  C21 UNL     1       0.778  -1.063   2.200  1.00  0.00           C  
HETATM   23  H1  UNL     1       5.253   2.013   3.273  1.00  0.00           H  
HETATM   24  H2  UNL     1       3.985   2.790   4.417  1.00  0.00           H  
HETATM   25  H3  UNL     1       2.245   2.315   2.966  1.00  0.00           H  
HETATM   26  H4  UNL     1       4.564   1.084   1.334  1.00  0.00           H  
HETATM   27  H5  UNL     1       3.278   1.965   0.496  1.00  0.00           H  
HETATM   28  H6  UNL     1       4.206  -0.595   2.437  1.00  0.00           H  
HETATM   29  H7  UNL     1       4.230  -1.372   0.398  1.00  0.00           H  
HETATM   30  H8  UNL     1       3.522  -0.049  -0.679  1.00  0.00           H  
HETATM   31  H9  UNL     1       2.268  -1.991  -1.359  1.00  0.00           H  
HETATM   32  H10 UNL     1       2.066  -2.494   0.348  1.00  0.00           H  
HETATM   33  H11 UNL     1       1.366   0.221  -0.933  1.00  0.00           H  
HETATM   34  H12 UNL     1      -0.670  -1.438   0.564  1.00  0.00           H  
HETATM   35  H13 UNL     1      -0.208  -1.650  -2.469  1.00  0.00           H  
HETATM   36  H14 UNL     1      -0.023  -2.909  -1.200  1.00  0.00           H  
HETATM   37  H15 UNL     1      -2.220  -2.636  -0.376  1.00  0.00           H  
HETATM   38  H16 UNL     1      -2.340  -3.101  -2.087  1.00  0.00           H  
HETATM   39  H17 UNL     1      -4.179  -2.046  -2.819  1.00  0.00           H  
HETATM   40  H18 UNL     1      -5.850  -0.124  -2.296  1.00  0.00           H  
HETATM   41  H19 UNL     1      -4.903   0.089  -3.785  1.00  0.00           H  
HETATM   42  H20 UNL     1      -4.475   2.208  -2.919  1.00  0.00           H  
HETATM   43  H21 UNL     1      -4.783   1.630  -1.262  1.00  0.00           H  
HETATM   44  H22 UNL     1      -2.315   1.011  -2.964  1.00  0.00           H  
HETATM   45  H23 UNL     1      -2.402   2.321  -1.697  1.00  0.00           H  
HETATM   46  H24 UNL     1      -3.070   0.457  -0.087  1.00  0.00           H  
HETATM   47  H25 UNL     1      -0.455   0.880  -1.349  1.00  0.00           H  
HETATM   48  H26 UNL     1      -1.647   0.831   1.454  1.00  0.00           H  
HETATM   49  H27 UNL     1      -1.150   2.180   0.446  1.00  0.00           H  
HETATM   50  H28 UNL     1       1.025   2.080   0.928  1.00  0.00           H  
HETATM   51  H29 UNL     1       0.318   1.325   2.428  1.00  0.00           H  
HETATM   52  H30 UNL     1       1.457  -1.011   3.075  1.00  0.00           H  
HETATM   53  H31 UNL     1      -0.237  -0.808   2.564  1.00  0.00           H  
HETATM   54  H32 UNL     1       0.772  -2.095   1.839  1.00  0.00           H  
CONECT    1    2    2   23   24
CONECT    2    3   25
CONECT    3    4   26   27
CONECT    4    5    6   21
CONECT    5   28
CONECT    6    7   29   30
CONECT    7    8   31   32
CONECT    8    9   21   33
CONECT    9   10   18   34
CONECT   10   11   35   36
CONECT   11   12   37   38
CONECT   12   13   13   17
CONECT   13   14   39
CONECT   14   15   40   41
CONECT   15   16   42   43
CONECT   16   17   44   45
CONECT   17   18   46
CONECT   18   19   47
CONECT   19   20   48   49
CONECT   20   21   50   51
CONECT   21   22
CONECT   22   52   53   54
END

HMDB0015500
     RDKit          3D
Allylestrenol
 54 57  0  0  0  0  0  0  0  0999 V2000
    4.2127    2.2854    3.5034 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2191    1.9970    2.6549 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4543    1.3069    1.3782 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7586    0.0075    1.3076 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2328   -0.7586    2.4054 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3520   -0.8145    0.1083 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1537   -1.6322   -0.3078 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1229   -0.5836   -0.2296 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2944   -0.9918   -0.3768 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5472   -1.9731   -1.4834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0316   -2.2998   -1.4259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8150   -1.0429   -1.6096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8977   -1.0858   -2.3592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8005    0.0466   -2.6590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2592    1.3752   -2.2264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7661    1.3360   -1.9811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4291    0.2370   -0.9915 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0181    0.3271   -0.5389 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8548    1.1179    0.7194 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5022    1.1861    1.3089 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.0555    1.1862 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7780   -1.0631    2.2002 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2535    2.0132    3.2729 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9850    2.7896    4.4171 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2454    2.3147    2.9659 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5641    1.0840    1.3336 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2779    1.9652    0.4955 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2059   -0.5951    2.4372 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2304   -1.3723    0.3981 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5221   -0.0494   -0.6789 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2680   -1.9913   -1.3594 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0665   -2.4944    0.3485 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3659    0.2212   -0.9325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6702   -1.4382    0.5644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2082   -1.6503   -2.4695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0229   -2.9086   -1.1997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2199   -2.6358   -0.3759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3403   -3.1010   -2.0866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1786   -2.0460   -2.8188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8496   -0.1241   -2.2958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9030    0.0888   -3.7849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4752    2.2084   -2.9193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7833    1.6299   -1.2620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3152    1.0112   -2.9640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4023    2.3212   -1.6975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0705    0.4570   -0.0869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4550    0.8798   -1.3490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6473    0.8307    1.4535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1499    2.1796    0.4459 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0247    2.0799    0.9278 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3183    1.3253    2.4282 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4572   -1.0112    3.0745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2372   -0.8084    2.5641 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7719   -2.0955    1.8391 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  1
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  1
 21  4  1  0
 21  8  1  0
 18  9  1  0
 17 12  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  6
  9 34  1  1
 10 35  1  0
 10 36  1  0
 11 37  1  0
 11 38  1  0
 13 39  1  0
 14 40  1  0
 14 41  1  0
 15 42  1  0
 15 43  1  0
 16 44  1  0
 16 45  1  0
 17 46  1  1
 18 47  1  6
 19 48  1  0
 19 49  1  0
 20 50  1  0
 20 51  1  0
 22 52  1  0
 22 53  1  0
 22 54  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Perselin	Kegg
Gestanin	HMDB
Gestanon	HMDB
Organon brand OF allylestrenol	HMDB
Allylestrenol organon brand	HMDB
Turinal	HMDB
Allyloestrenol	HMDB

Chemical Formula

C₂₁H₃₂O

Average Molecular Weight

300.4782

Monoisotopic Molecular Weight

300.245315646

IUPAC Name

(1S,2R,10R,11S,14R,15S)-15-methyl-14-(prop-2-en-1-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-ol

Traditional Name

gestanin

CAS Registry Number

432-60-0

SMILES

[H][C@@]12CC[C@@](O)(CC=C)[C@@]1(C)CC[C@]1([H])[C@@]3([H])CCCC=C3CC[C@@]21[H]

InChI Identifier

InChI=1S/C21H32O/c1-3-12-21(22)14-11-19-18-9-8-15-6-4-5-7-16(15)17(18)10-13-20(19,21)2/h3,6,16-19,22H,1,4-5,7-14H2,2H3/t16-,17+,18+,19-,20-,21-/m0/s1

InChI Key

ATXHVCQZZJYMCF-XUDSTZEESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as estrane steroids. These are steroids with a structure based on the estrane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Estrane steroids

Direct Parent

Estrane steroids

Alternative Parents

Substituents

17-hydroxysteroid
Hydroxysteroid
Estrane-skeleton
Delta-4-steroid
Tertiary alcohol
Cyclic alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

steroid (CHEBI:31189 )
Estrane and derivatives (C12811 )
C21 steroids (gluco/mineralocorticoids, progestogens) and derivatives (C12811 )
C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030125 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	80 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.00056 g/L	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00056 g/L	ALOGPS
logP	5.14	ALOGPS
logP	4.83	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Basic)	-0.17	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	93.14 m³·mol⁻¹	ChemAxon
Polarizability	37.17 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	173.009	31661259
DarkChem	[M-H]-	171.062	31661259
DeepCCS	[M-2H]-	212.593	30932474
DeepCCS	[M+Na]+	187.681	30932474
AllCCS	[M+H]+	180.0	32859911
AllCCS	[M+H-H2O]+	176.9	32859911
AllCCS	[M+NH4]+	182.8	32859911
AllCCS	[M+Na]+	183.6	32859911
AllCCS	[M-H]-	185.5	32859911
AllCCS	[M+Na-2H]-	185.8	32859911
AllCCS	[M+HCOO]-	186.3	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	7.96 minutes	32390414
Predicted by Siyang on May 30, 2022	20.8859 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.79 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2923.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	590.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	249.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	290.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	527.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	953.8 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	857.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	102.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1813.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	531.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1681.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	640.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	473.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	456.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	651.7 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Allylestrenol	[H][C@@]12CC[C@@](O)(CC=C)[C@@]1(C)CC[C@]1([H])[C@@]3([H])CCCC=C3CC[C@@]21[H]	2704.1	Standard polar	33892256
Allylestrenol	[H][C@@]12CC[C@@](O)(CC=C)[C@@]1(C)CC[C@]1([H])[C@@]3([H])CCCC=C3CC[C@@]21[H]	2434.8	Standard non polar	33892256
Allylestrenol	[H][C@@]12CC[C@@](O)(CC=C)[C@@]1(C)CC[C@]1([H])[C@@]3([H])CCCC=C3CC[C@@]21[H]	2398.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Allylestrenol,1TMS,isomer #1	C=CC[C@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CCCC[C@@H]4[C@H]3CC[C@@]21C	2519.4	Semi standard non polar	33892256
Allylestrenol,1TBDMS,isomer #1	C=CC[C@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CCCC[C@@H]4[C@H]3CC[C@@]21C	2783.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Allylestrenol GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-2390000000-f1adfe8dc88f417c8016	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Allylestrenol GC-MS (1 TMS) - 70eV, Positive	splash10-0a4l-2139000000-d46e49b4f8e43134ac8c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Allylestrenol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allylestrenol 10V, Positive-QTOF	splash10-0f89-0095000000-c48bafcafb6f4b6c1498	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allylestrenol 20V, Positive-QTOF	splash10-0fau-1291000000-4faba213d63885f04689	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allylestrenol 40V, Positive-QTOF	splash10-0gvx-3690000000-68f710c8eb72217aa2db	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allylestrenol 10V, Negative-QTOF	splash10-0002-0090000000-a3c48fa0a0a856ea2042	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allylestrenol 20V, Negative-QTOF	splash10-0002-0090000000-e64dacbcc5f01bdde97d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allylestrenol 40V, Negative-QTOF	splash10-0560-0090000000-39b8cd110e3c0ad19ccf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allylestrenol 10V, Positive-QTOF	splash10-0udi-0059000000-cc97fd004039cd495d4f	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allylestrenol 20V, Positive-QTOF	splash10-0ue9-0981000000-4bb685cf155da8a57b00	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allylestrenol 40V, Positive-QTOF	splash10-001i-9710000000-8450e6bf83763b7a76d3	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allylestrenol 10V, Negative-QTOF	splash10-0002-0090000000-afa15456ba65f9cea866	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allylestrenol 20V, Negative-QTOF	splash10-0002-0090000000-1bed2f4fbb78efad0384	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allylestrenol 40V, Negative-QTOF	splash10-0a4j-0090000000-a54f1ac1b9abf5592eab	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01431	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01431	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01431

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

205855

KEGG Compound ID

C12811

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Allylestrenol

METLIN ID

Not Available

PubChem Compound

235905

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

2. Progesterone receptor

General function:: Involved in sequence-specific DNA binding transcription factor activity
Specific function:: Isoform A is inactive in stimulating c-Src/MAPK signaling on hormone stimulation
Gene Name:: PGR
Uniprot ID:: P06401
Molecular weight:: 98980.0

References

Madauss KP, Stewart EL, Williams SP: The evolution of progesterone receptor ligands. Med Res Rev. 2007 May;27(3):374-400. [PubMed:17013809 ]
Gizard F, Robillard R, Gross B, Barbier O, Revillion F, Peyrat JP, Torpier G, Hum DW, Staels B: TReP-132 is a novel progesterone receptor coactivator required for the inhibition of breast cancer cell growth and enhancement of differentiation by progesterone. Mol Cell Biol. 2006 Oct;26(20):7632-44. [PubMed:17015480 ]
Wu HB, Fabian S, Jenab S, Quinones-Jenab V: Progesterone receptors activation after acute cocaine administration. Brain Res. 2006 Dec 18;1126(1):188-92. Epub 2006 Nov 15. [PubMed:17109827 ]
Boonyaratanakornkit V, McGowan E, Sherman L, Mancini MA, Cheskis BJ, Edwards DP: The role of extranuclear signaling actions of progesterone receptor in mediating progesterone regulation of gene expression and the cell cycle. Mol Endocrinol. 2007 Feb;21(2):359-75. Epub 2006 Nov 30. [PubMed:17138644 ]
Tranguch S, Smith DF, Dey SK: Progesterone receptor requires a co-chaperone for signalling in uterine biology and implantation. Reprod Biomed Online. 2006 Nov;13(5):651-60. [PubMed:17169175 ]
Bergink EW, Loonen PB, Kloosterboer HJ: Receptor binding of allylestrenol, a progestagen of the 19-nortestosterone series without androgenic properties. J Steroid Biochem. 1985 Aug;23(2):165-8. [PubMed:3928974 ]

Enzyme Details

3. Estrogen receptor

General function:: Involved in sequence-specific DNA binding transcription factor activity
Specific function:: Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Can activate the transcriptional activity of TFF1
Gene Name:: ESR1
Uniprot ID:: P03372
Molecular weight:: 66215.4

References

Kumar AS, Cureton E, Shim V, Sakata T, Moore DH, Benz CC, Esserman LJ, Hwang ES: Type and duration of exogenous hormone use affects breast cancer histology. Ann Surg Oncol. 2007 Feb;14(2):695-703. Epub 2006 Nov 14. [PubMed:17103262 ]
Lessey BA, Palomino WA, Apparao KB, Young SL, Lininger RA: Estrogen receptor-alpha (ER-alpha) and defects in uterine receptivity in women. Reprod Biol Endocrinol. 2006;4 Suppl 1:S9. [PubMed:17118173 ]
Yuri T, Tsukamoto R, Uehara N, Matsuoka Y, Tsubura A: Effects of different durations of estrogen and progesterone treatment on development of N-methyl-N-nitrosourea-induced mammary carcinomas in female Lewis rats. In Vivo. 2006 Nov-Dec;20(6B):829-36. [PubMed:17203775 ]
Montero Girard G, Vanzulli SI, Cerliani JP, Bottino MC, Bolado J, Vela J, Becu-Villalobos D, Benavides F, Gutkind S, Patel V, Molinolo A, Lanari C: Association of estrogen receptor-alpha and progesterone receptor A expression with hormonal mammary carcinogenesis: role of the host microenvironment. Breast Cancer Res. 2007;9(2):R22. [PubMed:17341305 ]
Ghebeh H, Tulbah A, Mohammed S, Elkum N, Bin Amer SM, Al-Tweigeri T, Dermime S: Expression of B7-H1 in breast cancer patients is strongly associated with high proliferative Ki-67-expressing tumor cells. Int J Cancer. 2007 Aug 15;121(4):751-8. [PubMed:17415709 ]
Csaba G, Gonda AI, Karabelyos C: Contraceptive treatment increases the affinity of uterine estrogen receptor in adult rat: perinatal gestagen treatment changes the reaction. Horm Metab Res. 1996 Jan;28(1):16-9. [PubMed:8820988 ]

Showing metabocard for Allylestrenol (HMDB0015500)

MOL for HMDB0015500 (Allylestrenol)

3D MOL for HMDB0015500 (Allylestrenol)

3D SDF for HMDB0015500 (Allylestrenol)

3D-SDF for HMDB0015500 (Allylestrenol)

PDB for HMDB0015500 (Allylestrenol)

3D PDB for HMDB0015500 (Allylestrenol)

SMILES for HMDB0015500 (Allylestrenol)

INCHI for HMDB0015500 (Allylestrenol)

Structure for HMDB0015500 (Allylestrenol)

3D Structure for HMDB0015500 (Allylestrenol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References